At what point does someone call it quits.

I understand the feeling. Sometimes I spend hours on getting user or root, my biggest weak points are dealing with web end points and using burp. Just the whole concept of it is confusing 2 me for some reason, my strongest points are priv esc especially when using something like LinPeas.sh Most of the time the exploits are SUIDs and I end up using GTFO bins to get an elevated shell. I guess my point is just keep going buddy, it may not seem like it at times but you are ahead than a lot of people in IT because I have seen sys/network admins underperform because they feel like what is in front of them is enough and they do not need to learn anything than that. That is a wrong boat to be on because IT in general is always about learning something new and hey man do not think that asking for help is bad, I do it a lot and sometimes I ask if they got what I got differently and how. It provides new knowledge. Just know we all feel like that at times.